I will never forget the morning I met my mentor for breakfast and put in my 2-weeks notice.

He had been my boss for almost four years.

I had gotten the job working for his ad agency through a mutual friend, and from the very beginning he treated me like his younger brother. On my first day of work, he invited me into his office so we could just talk and hang out. I wasn’t even sure what my job responsibilities were going to be, and neither did he. But he was doing a friend a favor, and I was there ready and eager to learn.

Over the course of those four years, we got to know each other extremely well. He took it upon himself to teach me things about the world nobody else had ever bothered to — like how white socks don’t go with black dress shoes (a mistake I made my first week of employment), or how to introduce yourself to the manager of a restaurant so they remember you by name.

My dad had always attended my hockey games growing up, always made sure there was food on the table and presents under the Christmas tree and that I could go anywhere I wanted for college. But aside from talking about grades, he wasn’t around much. He didn’t sit me down and explain to me what it meant to be a “man.” He didn’t walk me through the basics of adulthood, like how to get a credit card, how to open an IRA account for retirement, or how to buy my first share of stock. He didn’t cheers with me on my 21st birthday, or give me a call to see how I was doing after my girlfriend and I broke up.

But my mentor did.

When he looked at me, he said, he saw a younger version of himself — still unrefined, but someone with all the potential in the world.

He encouraged me to cut my hair — from long and wavy to short and clean. He took me out shopping and taught me what color shoes matched with what color pants, shirts, and belts. He took me all around the city of Chicago, popping into different restaurants and bars saying, “Now, if you really want to impress a girl, you take her here and order the ceviche appetizer. For dinner though…” — he’d walk back outside and point up the street — ”…you’ll want to take her up there.”

He took me to yoga workshops because he knew the value of staying centered and balanced. He took me to rooftop fashion shows and music festivals — always the VIP section. He took me to my first nightclub in Chicago, which I walked wide-eyed through while 100% sober (during these 4 years I didn’t drink a sip of alcohol, committed to my “bodybuilding” lifestyle). He brought me to meetings with other entrepreneurs, CEOs, potential and current clients. And he would always introduce me as his “Padawan,” a Star Wars reference he knew I enjoyed, painting the picture that he was the Jedi master and I was his young apprentice.

“You’re going to become a better version of me,” he’d say often — and I believed him.

The day I put in my 2-weeks notice was one of the scariest days of my entire life.

We met on the rooftop of Soho House Chicago, another spot (and private club) he had introduced me to. He had brought me to all their parties — Halloween, New Year’s Eve — and even gotten me a membership. I can’t walk into a Soho House in any city without thinking of my mentor and how many hours I spent listening to him in meetings there, soaking up as much knowledge as I could.

The night before, I had asked him if he’d be willing to meet for breakfast. He loved starting the work day with a cup of coffee on the roof.

When we sat down at the table, Chicago’s brisk summer sun coming up over the pool, he asked what was up, and I just started talking. And talking. I don’t even remember what I said, except for that I felt it was time I went my own way.

He didn’t get upset, or say anything for a while.

He just sat there, calm.

What made the whole thing so hard was that he had become so much more than just my “boss.”

To call him that would be to severely undermine how much we both cared about each other.

I wasn’t just putting in my 2-week’s notice. It felt like I was saying I didn’t want to be part of the family business. My leaving had a lot less to do with the actual day-to-day job responsibilities I held, and more to do with the dynamic shift from being his apprentice to becoming my own individual.

After a long while, he shared his thoughts. He was supportive — sad to see me go, but more than that, excited for what the future held. If things didn’t go as planned, there would be a job waiting for me in a few months, if I wanted it.

He asked for the bill and said he was going to take the rest of the day off.

“Today is a sad day,” he said, as we got up from the table to walk to the elevator.

As we were waiting for the *ding* he asked what I planned to do, now that I was going off on my own.

“I’m going to write,” I said. “Maybe become an entrepreneur, I don’t know yet.

And I didn’t know — not really. All I knew was that it was time I take the leap.

“Well, if you do become an entrepreneur,” he said, “here are some words of advice: When everyone is rattled by the storm, you have to bring the calm.When everyone else gets stressed, you have to stay cool, calm, and collected. When everyone is freaking out, you have to reassure them. When there is doubt, you have to bring certainty.”

*Ding*

We rode the elevator down in silence.

I didn’t understand what he meant that day.

18 months and 8 full-time employees at Digital Press later, now I understand.

When you’re building a company, your team, it’s culture, and the way you perform the work you do is all a reflection of the founder(s).

Which means, as the founder, “When everyone is rattled by the storm, you have to bring the calm.”